IL23180A - Process for the manufacture of delta4 and delta1,4-9beta,10alpha-steroids of the androstane and pregnane series - Google Patents
Process for the manufacture of delta4 and delta1,4-9beta,10alpha-steroids of the androstane and pregnane seriesInfo
- Publication number
- IL23180A IL23180A IL23180A IL2318065A IL23180A IL 23180 A IL23180 A IL 23180A IL 23180 A IL23180 A IL 23180A IL 2318065 A IL2318065 A IL 2318065A IL 23180 A IL23180 A IL 23180A
- Authority
- IL
- Israel
- Prior art keywords
- hydroxy
- hydrogen
- lower alkyl
- esterified
- halogen
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 35
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- QZLYKIGBANMMBK-UGCZWRCOSA-N 5α-Androstane Chemical compound C([C@@H]1CC2)CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CCC[C@@]2(C)CC1 QZLYKIGBANMMBK-UGCZWRCOSA-N 0.000 title claims 2
- 150000003128 pregnanes Chemical class 0.000 title claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 47
- 150000001875 compounds Chemical class 0.000 claims description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 13
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 claims description 11
- 229910052736 halogen Chemical group 0.000 claims description 10
- 150000002367 halogens Chemical group 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- -1 alkyl ethynyl ketone Chemical compound 0.000 claims description 3
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- 150000002596 lactones Chemical class 0.000 claims description 3
- 150000002431 hydrogen Chemical group 0.000 claims 16
- 238000006482 condensation reaction Methods 0.000 claims 6
- 125000004414 alkyl thio group Chemical group 0.000 claims 4
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 3
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 238000009833 condensation Methods 0.000 description 14
- 230000005494 condensation Effects 0.000 description 14
- 239000007858 starting material Substances 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 11
- 150000003431 steroids Chemical class 0.000 description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- JLIDVCMBCGBIEY-UHFFFAOYSA-N 1-penten-3-one Chemical compound CCC(=O)C=C JLIDVCMBCGBIEY-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000011909 oxidative ring-opening Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000026030 halogenation Effects 0.000 description 2
- 238000005658 halogenation reaction Methods 0.000 description 2
- 239000000583 progesterone congener Substances 0.000 description 2
- 238000000197 pyrolysis Methods 0.000 description 2
- 230000003637 steroidlike Effects 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- ABAFKQHGFDZEJO-UHFFFAOYSA-N 4,6,6-trimethylbicyclo[3.1.1]heptane-4-carbaldehyde Chemical compound C1C2C(C)(C)C1CCC2(C)C=O ABAFKQHGFDZEJO-UHFFFAOYSA-N 0.000 description 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- 241000186704 Pinales Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 230000001195 anabolic effect Effects 0.000 description 1
- 150000001441 androstanes Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- IFNMFFFINNZGER-UHFFFAOYSA-N hexa-1,5-dien-3-one Chemical compound C=CCC(=O)C=C IFNMFFFINNZGER-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical compound C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 description 1
- 238000006552 photochemical reaction Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000001072 progestational effect Effects 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/185—Saturated compounds having only one carboxyl group and containing keto groups
- C07C59/215—Saturated compounds having only one carboxyl group and containing keto groups containing singly bound oxygen containing groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
- C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
- C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
- C07C309/66—Methanesulfonates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/72—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/73—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/14—Benz[f]indenes; Hydrogenated benz[f]indenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/16—Benz[e]indenes; Hydrogenated benz[e]indenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US400206A US3412107A (en) | 1964-09-29 | 1964-09-29 | 11-hydroxy-5-oxo-3, 5-seco-a-nor-androstan-3-oic acid 3, 11-lactones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL23180A true IL23180A (en) | 1969-09-25 |
Family
ID=23582655
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL23180A IL23180A (en) | 1964-09-29 | 1965-03-18 | Process for the manufacture of delta4 and delta1,4-9beta,10alpha-steroids of the androstane and pregnane series |
| IL31354A IL31354A (en) | 1964-09-29 | 1965-03-18 | Tricyclic steroid intermediates and processes for their preparation |
| IL31353A IL31353A (en) | 1964-09-29 | 1965-03-18 | 3,5-seco-a-nor-steroids of the androstane and pregnane series |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL31354A IL31354A (en) | 1964-09-29 | 1965-03-18 | Tricyclic steroid intermediates and processes for their preparation |
| IL31353A IL31353A (en) | 1964-09-29 | 1965-03-18 | 3,5-seco-a-nor-steroids of the androstane and pregnane series |
Country Status (14)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3761503A (en) * | 1964-09-29 | 1973-09-25 | Hoffmann La Roche | Substituted-3,5-seco-a-nor-pregnan-3-oic-acids |
| DE2331997A1 (de) * | 1973-06-21 | 1975-01-16 | Schering Ag | Verfahren zur herstellung von bicycloalkan-derivaten |
| CA1195997A (en) * | 1979-02-23 | 1985-10-29 | Andor Furst | Dea-steroids |
| FR2500441A1 (fr) * | 1981-02-23 | 1982-08-27 | Roussel Uclaf | Nouveaux medicaments derives de la 3-hydroxy dodecahydro benz (e) inden-7-one, produits derives de la 3-hydroxy dodecahydro benz (e) inden-7-one et leur procede de preparation |
| DE3434451A1 (de) * | 1984-09-20 | 1986-03-27 | Austgen, René, 6625 Püttlingen | Dieselkraftstoff-filter |
-
1964
- 1964-09-29 US US400206A patent/US3412107A/en not_active Expired - Lifetime
-
1965
- 1965-03-18 IL IL23180A patent/IL23180A/en unknown
- 1965-03-18 IL IL31354A patent/IL31354A/en unknown
- 1965-03-18 IL IL31353A patent/IL31353A/en unknown
- 1965-03-25 CH CH760568A patent/CH577446A5/de not_active IP Right Cessation
- 1965-03-27 DE DE1618507A patent/DE1618507C3/de not_active Expired
- 1965-03-27 DE DE19651618508 patent/DE1618508A1/de active Pending
- 1965-03-27 DE DE1518980A patent/DE1518980C3/de not_active Expired
- 1965-03-29 GB GB36706/67A patent/GB1103988A/en not_active Expired
- 1965-03-29 GB GB36700/67A patent/GB1103982A/en not_active Expired
- 1965-03-29 GB GB36703/67A patent/GB1103985A/en not_active Expired
- 1965-03-29 GB GB36701/67A patent/GB1103983A/en not_active Expired
- 1965-03-29 SE SE10751/69A patent/SE353905B/xx unknown
- 1965-03-29 GB GB36702/67A patent/GB1103984A/en not_active Expired
- 1965-03-29 GB GB13173/65A patent/GB1103574A/en not_active Expired
- 1965-03-29 SE SE4026/65A patent/SE317968B/xx unknown
- 1965-03-29 AT AT282365A patent/AT280489B/de active
- 1965-03-29 GB GB36705/67A patent/GB1103987A/en not_active Expired
- 1965-03-29 GB GB36704/67A patent/GB1103986A/en not_active Expired
- 1965-03-29 SE SE10752/69A patent/SE353904B/xx unknown
- 1965-03-30 NO NO157467A patent/NO125273B/no unknown
- 1965-03-30 ES ES0311225A patent/ES311225A1/es not_active Expired
- 1965-03-30 FI FI0765/65A patent/FI42552B/fi active
- 1965-04-29 BE BE663197A patent/BE663197A/fr unknown
-
1968
- 1968-12-13 DK DK609968AA patent/DK126031B/da unknown
- 1968-12-13 DK DK610168AA patent/DK123234B/da unknown
- 1968-12-13 DK DK610268AA patent/DK123235B/da unknown
-
1969
- 1969-02-05 NL NL6901813A patent/NL6901813A/xx unknown
- 1969-02-05 NL NL6901812A patent/NL6901812A/xx unknown
- 1969-03-24 FI FI0854/69A patent/FI43590B/fi active
- 1969-03-24 FI FI0857/69A patent/FI43592B/fi active
- 1969-03-24 FI FI0856/69A patent/FI43591B/fi active
- 1969-03-24 FI FI0858/69A patent/FI43593B/fi active
- 1969-03-24 FI FI0859/69A patent/FI43594B/fi active
- 1969-12-31 MY MY196982A patent/MY6900082A/xx unknown
- 1969-12-31 MY MY196976A patent/MY6900076A/xx unknown
- 1969-12-31 MY MY196983A patent/MY6900083A/xx unknown
- 1969-12-31 MY MY196981A patent/MY6900081A/xx unknown
- 1969-12-31 MY MY196977A patent/MY6900077A/xx unknown
- 1969-12-31 MY MY196980A patent/MY6900080A/xx unknown
- 1969-12-31 MY MY196979A patent/MY6900079A/xx unknown
- 1969-12-31 MY MY196978A patent/MY6900078A/xx unknown
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